When you bet your heart
by 10thandrose
Summary: you better be prepared to bleed. A Dair girl's wish post Dair kiss.
1. When you bet your heart

When you bet your heart, you better be prepared to bleed

(A/N: I only recently began watching GG again... after I saw them taking B&D in this direction. Forgive me if I don't include much of the other characters... The directions they have gone in on the show just bore me. And really, if you're reading this, I hope you share my thoughts on Dair. Otherwise I fear you'll be disappointed. :) And I'm sure I'm way off base on what will happen, but this is what would happen if I was steering this tugboat.)

{Immediately post kiss…}

Blair knew she should be disgusted. Cabbage Patch? Seriously? But of their own volition, her hands moved from his lapel to tangle in the soft hair at his neck. An infinite moment passed as she reveled in the act of kissing and being thoroughly kissed before she thought, "No wonder Serena kept going back to him… Serena…" Blair's eyes shot open and she began to push him away. Dan's hands stayed where they were, one on the side of her neck and the other on her lower back, brushing the tips of her hair. With a little distance between them, Blair tried to breathe normally again.

"There," she said, wishing her voice sounded steadier, "now we've proven Rufus and Dorota wrong. You can scurry back to Brooklyn, convinced that there's nothing between us."

Dan's eyes widened a bit. "Did you just black out? That most certainly was not nothing."

"Look Humphrey, I'm sure you've had years to contemplate kissing me, but I assure you, on this side of the bridge, it was nothing."

"Certainly, your breathing is accelerated, you're trembling and blushing, but I'm sure that is just a testament to your ambivalence. May I remind you, you were the one that pulled me closer," Dan replied coolly.

"To prove a point, but if you want to read something into it, there is something between us, and it better be the distance between Manhattan and Brooklyn!" she shouted.

"I'm going," he said looking a bit conflicted, "but before I do, I just want to remind you…"

Before Blair could contemplate saying "of what?" he had his body pressed flush against hers and was kissing her with such force that her back arched. She was breathless and therefore silent as he pulled away. He spared only a moment to look into her eyes before storming out of the penthouse.

* * *

><p>Dan never imagined kissing Blair would feel the way it had. Well, before tonight, he had never really imagined kissing Blair, but he couldn't deny that he figured it would be something akin to kissing a statue. Not much reaction from the kissing partner. Especially if she was kissing him.<p>

So when she pulled him to her, he acceded how wrong he truly was. He had wrapped one arm around her tiny waist and the other from her now strapless shoulder to her neck, when she began to disengage. Still he didn't let her go, if only because he was surprised how much he liked having her in his arms. So his shock when she turned, before his eyes, into the Blair he loved to loathe in high school was obvious. Under normal circumstances, he would not yell at someone he had just kissed, but damn it, she infuriated him. Thinking of it now, it seemed to follow the system of their relationship. Fighting with Blair was second nature at this point. He probably should not have kissed her a second time though. But somehow her denial, made him more determined to convince her. And if a small part of him thought the first kiss was simply a fluke, well he would have been disappointed. After he pulled away, he couldn't help but stare, hoping he had made a dent, but all he saw was shock. It was all he could do to leave without another word.

He left the building in a sort of daze, and truthfully couldn't remember making it home. But somehow he walked into the loft, undressed, fell into bed, and tried desperately not to think of Blair Waldorf. A more useless endeavor had never been attempted. Tossing and turning all night, he decided he would corner her soon and demand she admit that she had felt something.

* * *

><p>She lay in bed, her hair artfully arranged on the pillow. <em>Okay<em>, she thought, _you can think about the kiss tonight, because that's all you get. Tomorrow, we're back to hating Humphrey and we must never think about it again._ So that's how Blair passed the night. Imagining the tenderness in his hands brushing her shoulder, how she had responded to him in ways Blair Waldorf should never respond to anyone from Brooklyn. Part of her was disgusted at herself for even this small luxury. The rest of her wished for the very first time, that she was anyone but Blair Waldorf so she could give Humphrey a chance.

The next morning Blair put on her favorite spring dress (this season), and expertly applied under eye concealer. She yelled to Dorota that she was going out for coffee.

She had no more ordered and sat down, than Dan had dropped into the chair across from her.

"What the hell are you doing here Humphrey?" she whispered.

"Well, before you start yelling at me, I just wanted to see you and I figured this was the easiest, and least conspicuous way," he said, reaching across the table to brush her fingers with his. She pulled away quickly, but he could see she was conflicted.

"You have to leave. No one can see us together."

"Relax Blair, if anyone asks, I was on my way to check on Serena after last night's thing with Lily, and ran into you. But I'm serious, we need to talk. I'm not going to let you pretend that nothing happened," he said simply.

"Oh, come off it, Humphrey. We both know you're still in love with Serena, and I love Chuck."

"You're wrong. I am over Serena. It was something you said actually, on our ill fated road trip, that made me start to see it. And you are over Chuck, in your own way. Of course you still care for him, but you've also realized that Blair Waldorf won't continue to put someone first in her life, when she is never first in theirs. We could be that for each other. We do like the same things-"

"Fashion, the subway," she interrupted.

"Art, classic literature, movies that are older than we are," he countered. "We could be good together."

"Oh please, Humphrey, we fight all the time now. Imagine if we spent any more time together. New York would start to look like Post World War II Europe."

"Well, of course we would have to agree not to use nuclear weapons. Usable force," he replied smirking. "I think we should go out," Dan began at the same moment that Blair said,

"I think we should have sex."

Dan wouldn't have been more shocked if she had suggested they go spend the day at Walmart. "Didn't you just say you didn't even enjoy kissing me? What could possibly prevail on you to sleep with me?"

"No sleeping Cabbage Patch. Just sex. One time. Get it out of our systems, and I'm sure, we'll be content to never see each other again," she posited.

"Really," he laughed. "Just like our one kiss? What happens if you like it?" he asked smirking.

"Don't flatter yourself. How does tonight work for you?" she asked looked rather serious.

"You're serious? Okay, one condition… if after, you do still want to see me, even just a little bit, you have to let me take you on a date. If you want, we can even concoct a scenario to explain it to everyone," Dan suggested.

"I agree to your terms only because I know it will never happen. I am also delighted that you have taken my scheming lessons to heart," she smiled.

Dan simply laughed in response.

"8 o'clock at the loft?" she asked tentatively.

Dan nodded his assent. "Do you need any special considerations? Silk sheets, breakfast at tiffany's playing in the background…"

"A shower would be nice," Blair interrupted.

"I'm sure I can oblige you. I should go. I have exceeded the amount of time allotted for polite conversation. See you."

Blair nodded as he walked away. The unspoken 'tonight' chiming in her ears even though he did not say it.

* * *

><p>She elected to skip her only class of the day, knowing her mind would be too preoccupied with her coming tryst to concentrate on art history. Instead she went back to the penthouse and did nothing all day. When it came time to get ready, she faced a moral quandary. She did not want Brooklyn to think she was dressing up to try to impress him. She knew she had to wear the same dress as he saw her wearing this morning. But she was concerned about the undergarment situation. She usually just chose based on the neckline of her ensemble. Unfortunately, today it was a frothy, black lace confection that Humphrey would certainly believe was for his benefit. She decided to change it for a pink floral bustier set that was too girly to really be alluring.<p>

She spared herself a look in the mirror and a fluff to her hair before walking out the door and hailing a cab to Brooklyn. She was unsurprised that the door was unlocked. She let herself in, and her eyes found Humphrey. She smiled as she saw him smooth his hair back nervously as he turned to her. It lightened her spirit that he seemed nervous.

He cleared his throat and asked, "Can I get you anything? Something to drink?"

Blair shook her head no. When it appeared he was going to continue is nervous rambling, she put her hand up to silence him. "We both know why I'm here. Shall we dispense with the formalities?"

When Dan smirked and shrugged in response, she unzipped her strapless dress and let it fall to the floor. She tried not to be pleased at his reaction. _Every girl wants to feel desirable_, she thought. _Doesn't mean anything._

Wearing her underwear and the flesh colored pumps that coordinated so beautifully with the dress now in a puddle on the floor of a Brooklyn loft, she led him to the bedroom. She sat down on the bed and crossed her arms. She realized, belatedly, that she was giving him an eyeful of cleavage, but she persisted. Breaking the silence, she said, "I think you are entirely too clothed for the purpose of this visit."

Smiling ruefully, he untucked and unbuttoned his shirt. He moved toward the bed without going any further. She would never admit that she found his abs rather attractive.

He knelt by her legs and she couldn't resist the urge to say, "I prefer you this way."

"On my knees and shirtless?" he asked.

"At my feet and silent," she countered.

He gently removed her shoes before kissing his way up both legs. Then he sat behind her on the bed, gently pushing her hair over one shoulder, he kissed her neck and shoulders until she was sagging against him. Finally, he began to undo the hook and eye closures that held her bustier together. She looked over her shoulder as he kissed his way down her bare back.

That was the end for her. She could take no more of such tenderness. She threw the now loose bustier across the room, and turned in to his embrace. And she would have made him stop taking it slow, but for once, Blair Waldorf was not in control. And maybe that scared her, but there was something so powerful about Humphrey's silent refusal to change his pace. He laid her gently against the pillows and continued his ministrations on her arms and chest and stomach. How he tortured her.

Finally he put his lips to hers, and the unconscious sigh of relief did what she had found impossible, made him move faster. Before she realized, he was before her, as she was, both naked and needy, and however unlikely, desperate for the other. He stood there a moment too long, and she whispered, "Dan." And whether it was the vulnerability in her voice or the fact that up to this point, she had not said his name, he forgot whatever plan he had in mind to drive her crazy and make her beg for him to make love to her. He knelt on top of her, and brushed the hair off her face. He kissed her gently, and interlaced their fingers. All the while Blair was ready to yell at him. He was still stalling, and she was about to open her mouth to say so, when he entered her, and the protest became a moan that she could not stifle. So much buildup she was already panting with release. Dan held her closer and kissed her temple as she came down. Their lovemaking continued until she screamed his name. Just once, and she heard her name whispered from his lips. Both too exhausted to ponder it any further, they fell asleep in each others' arms.


	2. What if I was the one

What if I was the one that you warned me about?

(A/N: The fic title and the chapter title are both pilfered from a Cross Canadian Ragweed song. I may stick with lyrics as titles because every song I hear lately makes me think of these two. Gah.)

She woke up the next morning to him kissing each finger on her hand. She squeezed her eyes shut, so he would continue.

"I know you're awake," he whispered into her palm.

"No, I'm not," she groaned. "How did you know?"

"Your breathing changed," he said.

She inched up so that her lips were closer to his, and she was just about to kiss him when he pulled back.

"When are you going to let me take you out?" he asked, his face only centimeters from hers.

"Who said I was going out with you?" she replied, coyly.

"You lost our bet because of the mind-blowing sex," he murmured confidently.

"Mind blowing?" she scoffed.

"Yes. I am certain anything less and you would be gone by now. Out the door, down the street, at the penthouse, gone. And yet, here you are." He gently traced her cheek and his voice took on a more vulnerable note, "I must have done something right."

She closed the distance between them and kissed his mouth forcefully. "You're a little right. Help me put myself back together," she said, grabbing her bustier off the floor. She pulled on the bottoms, and knelt on the bed, holding the bustier in place so Dan could fasten the numerous hook and eyes that secured it.

He wasn't even halfway done when he remarked, "Blair, if this had gone differently, how would you have ever gotten yourself trussed back up in this?"

"I'd have called Dorota, or gone without, I suppose," she replied off hand.

His voice became deeply seductive as he asked, "Does that happen often?"

She looked over her shoulder at him, and replied, "Occasionally."

He caught her lips and was about to remove the little of the top he had actually secured, when she said, "You have some scheming to do."

"You are correct," he groaned.

"So tell me. I want to hear about Dan Humphrey's brilliant scheme."

"Oh, you'll see."

* * *

><p>The next day, Dan was spending the afternoon with Eric, who was regaling him with tales of the best Pork Osso Bucco ever.<p>

"It seems pretty easy, I bet I could make Pork Osso Bucco," Dan said confidently.

"Please," Eric rolled his eyes, "we all know your talents in the kitchen are woefully limited."

"Really, I bet you dinner at this place that I can make a mean Pork Osso Bucco."

"What do I get when you inevitably lose?" Eric asked.

"Something to embarrass me and make sure I never challenge you again?"

"Of course," Eric replied. "I can't think of anything bad enough."

"Oh, I've got it, how about this," posited Dan, "if I lose, I'll ask Blair on a date?"

"Oh my God," Eric said, laughing hysterically.

Dan had never tried to lose so hard in his life, and failed at Pork Osso Bucco spectacularly.

"Now, Eric, if she says no, that's that, right? I mean, you don't want me to stalk her, right?" Dan said, sounding more worried than he really was.

"As entertaining as that would be, how about I just make sure she says yes?" he replied taking his phone out of his pocket and dialing Blair.

"YOU WOULDN'T!" Dan yelled playfully.

"Blair, it's Eric," he said with his hand up to shield him from Dan. "I have a favor to ask… No, no hostile takeover, but something interesting. Dan just embarrassed himself horribly in the kitchen and in so doing lost a bet. As penance he has to ask you out, but I think you should say yes, and then make him miserable the whole night."

Dan groaned audibly in the background.

"Just because I love you darling. Tell him to call and let me know when," she said laughing.

Later that day, a Gossip Girl Blast let all of New York know about the impending Humphrey-Waldorf date.

_Oh Boys and Girls, there are some things yours truly never thought she'd say…  
>Here's one of them:<br>We're in for a long hot summer if this is how it's getting kicked off.  
>I'm all for starting with a bang,<br>But Lonely Boy and Queen B just set off the atomic bomb.  
>Have fun on your date.<em>

* * *

><p>Thus, two nights later, Dan picked her up looking better than she thought jeans could. She of course was wearing a patterned pencil skirt and a green silk blouse.<p>

"You look beautiful," he said. "Are you ready for our date?"

"Of course. Where are we going?" she asked.

"Not far for now, we're going to the Morgan."

"But, it's after 6," she replied, not knowing whether to be disappointed or irritated that Humphrey had not adequately planned. "It's closed."

"So you think," he replied cryptically.

When they reached the Morgan, an attractive woman opened the door for them. "Dan it's always a pleasure, do tell your father I said hello."

"Isabelle, this is Blair Waldorf. Blair, this is Isabelle Dervaux, she's the curator, and an old friend of my father's."

Blair swallowed her shock enough to politely say hello.

"Dan, you know the rules, just let yourself out when you're done," Isabelle said, winking.

And then they were alone. Blair cleared her throat, "So what are we here to see?"

"You should know," he replied leading her to the wing where the Degas exhibition was. "Tonight was the last night, and tomorrow, all this will be on a plane going somewhere new. I just wanted you to get to see it, since I gave you such a hard time about it before..." he trailed off.

She reached for his hand, and led him to the first piece. It was comfortable walking through the exhibition with Humphrey. He didn't try to rush her and she didn't protest if he lingered at a piece she was less interested in. They barely spoke until she saw "Two Dancers on Stage."

"You see the movement? I almost expect her to grande jete any moment," she said wistfully.

He pointed toward "Dancers Pink and Green," and said, "Don't you own that dress?"

She smacked him on the arm lightly, before nodding thoughtfully. "Maybe."

When they were walking out of the Morgan, she turned to him. "I really enjoyed this. I know everyone listens to me, but sometimes I think they ignore what I'm saying. So thank you, for realizing how much I wanted to see this."

"We're not done Waldorf. On to dinner," he replied hailing a taxi.

"Dinner? Where?" she asked.

"A top secret location, far away from the prying eyes of Manhattan's eye in the sky," he said with a devious laugh.

"We're going to Brooklyn," she guessed confidently.

He gave the driver the address to the loft, and just smiled at her curious stare.

They walked into the loft, and he snatched a few containers from the kitchen. One he handed to her and one he used an oven mitt to carry. Then he led her to the rooftop terrace.

She was speechless. He had set up a café style table with dinnerware and a vase with a pink rose. And all along the railing, he had strung white twinkle lights.

"Generally I'd make a snide comment about Christmas lights in May, but this is kind of gorgeous. What's for dinner?" she said smiling.

"Well, I had to redeem myself so it's your favorite salad (I asked Dorota) and Pork Osso Bucco, which went really badly the first time, but I think I've worked the kinks out," he smirked.

She got the feeling she was missing a critical part of the joke, but ignored it, as he pulled her chair out for her. Then he served them both, and sat down across from her.

"It's delicious," she said quickly. "Why did you go to all this trouble though? I mean, you know I would have been happy with takeout."

"Happy?" he asked, raising his eyebrows.

"Well, it's what I was expecting," she said.

"And that is why I didn't. Nothing about us is expected, so why should my behavior be. And, I know you could get a million guys to take you to naboo or whatever the 'it' restaurant is today, but I had a sneaking suspicion that no guy had ever gone to the trouble of making you dinner. I don't want to be just one of the millions, I want to be somebody important to you," he said, rambling nervously.

"It's Nobu, and I can tell you, no one has ever tried so hard. I'm genuinely impressed," she replied.

"Wow, was that a compliment? And the night's not even over…" he said, cryptically.

He stood, and put his napkin aside. "Blair Waldorf, park avenue princess, dictator of taste, would you do me the honor of a dance?"

"But there isn't any music?" she protested.

He pulled a tiny remote out of his pocket and pressed a button. Soft music filtered over the terrace, "Any more objections?"

She just put her hand in his and they danced softly in the spring breeze. After a moment, she laid her head on his shoulder and whispered, "I wish tonight didn't have to end."

"Hmm?" Humphrey asked softly.

"I wish I could just stay here with you… but as far as anyone knows, it's our first date, and they'll be watching for us," she said, thinking out loud. "How do you feel about tonight being our first PDA?" she asked tentatively.

"Explain."

"Well, if Gossip Girl just happened to catch us having a chaste kiss tonight and a more passionate kiss our next date, then after that everyone will assume I succumbed to your charm and fell into bed with you," she elaborated. "Then I can run away to Brooklyn and never return."

"Brooklyn should be so lucky," he chuckled.

"You bet your sweet ass," she smirked.

"Waldorf, the language!" he exclaimed, but then he tried, covertly to check his ass out.

She interrupted this by kissing him fervently.

"What was that for? Not that I'm complaining," he asked.

"Because I'll have to restrain myself later," she replied.

"You have to restrain yourself around me?" he asked, smirking.

"Not in Brooklyn, which is why I'm texting Gossip Girl to tell her we're leaving the loft. And, don't get cocky… it's not becoming," she scolded good-naturedly.

"You know, I really like this plan. Gossip Girl has been taking advantage of us for years. It's about time we got something out of this twisted relationship," Dan said, lightly.

"She did help us with Juliet as well," Blair reminded him.

"That's true," he replied.

* * *

><p>On the cab ride to the penthouse, Blair asked, "Have you thought about your chaste kiss coming up?"<p>

He reached for her hand, and said, "Don't worry. I have a plan."

"That scares me Humphrey," she said laughing.

He smiled, and she couldn't hold it in anymore, she kissed him in between laughing.

It was the shortest ride from Brooklyn ever, spent kissing Blair. When he walked her to the door, she was unable to keep the smile off her face. "I hope we can do this again soon," she said gazing at him.

He took her hand and brought it to his lips. Blair blushed and then after a moment, reached up and gave him a gentle 'first kiss.'

"Call me," she whispered as she pulled away.

Dan took the cab back to Brooklyn, and as soon as he was back in the loft, he dialed Blair on his cell.

"Have you looked at Gossip Girl?" she asked, in way of greeting.

"No, I just walked in," he replied.

"Pull it up, Humphrey. You're gonna love this."

_Chivalry is not dead, boys and girls,  
>It's just been living in Brooklyn.<em>

This was followed by four pictures of them. One of him walking her to her door, Blair smiling brilliantly, one of him kissing her hand, one of her reaction and finally one of their 'first' kiss.

_I think we're going to have to change Lonely Boy's designation  
>from paupersquire to white night._

_Xoxo Gossip Girl_

"So this brings me to my next question, could we negotiate our next date?" At Dan's laugh, Blair continued, "Mother is having a party to celebrate her spring line. A Pink Party. How do you feel about formal?"

"I could be amenable. Provided the second phase of our plan is still intact," he replied.

"Naturally. I've always preferred kissing in couture," she sighed.

"I wish I could say I was surprised," he laughed.

"I wish I was in Brooklyn," she whispered.

"Just think," he said cheerfully, "one more date and we're home free. Then you can move in," he chuckled. "Once you get over your aversion to Brooklyn that is."

"Two things, Humphrey. One, your closet is woefully inadequate to house my shoes, and two I'm working on my aversion. We'll simply have to work out a system," she reprimanded.


End file.
